Stereochemistry and Reactions of Aziridinyl-phosphinothionates Derived from Amino Acids

Akinori Hirashima, Morifusa Eto

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Aziridinylphosphinothionates were prepared from optically active ethyl hydrogen phenylphos-phonothionates and l-bromo-2-alkanamines derived from leucine or valine. The aziridine ring was opened by the action of some nucleophiles. Refluxing the aziridinylphosphinothionates in acetone with sodium iodide caused hydrolysis accompanied by the rearrangement of the sulfur atom to give β-mercaptoethylphosphonamidates. The reaction mechanism was discussed with stereochemical considerations. The insecticidal activity of the products was also examined.

Original languageEnglish
Pages (from-to)829-838
Number of pages10
JournalAgricultural and Biological Chemistry
Volume47
Issue number4
DOIs
Publication statusPublished - Jan 1 1983

Fingerprint

Sodium Iodide
Nucleophiles
Stereochemistry
reaction mechanisms
stereochemistry
Valine
iodides
valine
Acetone
Sulfur
Leucine
acetone
hydrogen
leucine
Hydrogen
Hydrolysis
sulfur
hydrolysis
sodium
Amino Acids

All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)
  • Agricultural and Biological Sciences(all)

Cite this

Stereochemistry and Reactions of Aziridinyl-phosphinothionates Derived from Amino Acids. / Hirashima, Akinori; Eto, Morifusa.

In: Agricultural and Biological Chemistry, Vol. 47, No. 4, 01.01.1983, p. 829-838.

Research output: Contribution to journalArticle

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